Alkaloids
First published: 15 June 2010
Abstract
The article contains sections titled:
1. |
Introduction |
2. |
Alkaloids Derived from Polyketides and the Amino Acids Ornithine and Lysine |
2.1. |
Alkaloids Derived by the Insertion of Nitrogen into a Polyketide |
2.1.1. |
(S)-(+)-Coniine, γ-Coniceine and Related Alkaloids |
2.1.2. |
Solenopsin Family (Fire Ant Alkaloids) |
2.1.3. |
Perhydroazaphenalenes: Defensive Alkaloids of the Coccinellidae |
2.1.4. |
Cyanobacteria Alkaloids |
2.1.5. |
Additional Polyketide-Derived Alkaloids |
2.2. |
Alkaloids Derived from Ornithine and/or Arginine |
2.2.1. |
Tropane Alkaloids |
2.2.2. |
Pyrrolizidine Alkaloids |
2.3. |
Alkaloids Derived from Ornithine (and/or Arginine) and Nicotinic Acid |
2.4. |
Alkaloids Derived from Lysine (Lys, K) and Nicotinic Acid |
2.5. |
Purine Alkaloids |
2.6. |
Imidazole Alkaloids |
2.7. |
Pepper Alkaloids |
3. |
Alkaloids Derived from the Shikimate Pathway |
3.1. |
Alkaloids Derived from Anthranilate |
3.2. |
Alkaloids Derived from Phenylalanine and Tyrosine |
3.2.1. |
Biosynthesis of Dopamine, Mescaline and Capsaicin |
3.2.2. |
Biosynthesis of Tetrahydroisoquinoline Alkaloids |
3.2.3. |
Cryptostyline (Orchidaceae) and Alkaloids of the Amaryllidaceae |
3.2.4. |
Ephedra Alkaloids |
3.3. |
Alkaloids Derived from Tyrosine |
3.4. |
Alkaloids Derived from Tryptophan and/or Tryptamine (Indole Alkaloids) |
3.4.1. |
Alkaloids Derived from Tryptamine and an Unrearranged Monoterpene Unit |
3.4.2. |
Mold Metabolites |
3.4.3. |
Ergot Alkaloids |
3.4.4. |
Corynantheine–Heteroyohimbine Structural Types |
3.4.5. |
Corynantheine-Type Alkaloids |
3.4.6. |
Ajmalicine-Type Alkaloids |
3.4.7. |
Heteroyohimbine Oxindole Type |
3.4.8. |
Glucoalkaloids |
3.4.9. |
Yohimbine–Reserpine Structural Types |
3.4.10. |
Akuammidine–Quebrachidine–Ervatamine–Gelsemine–Akuammiline Structural Types |
3.4.11. |
Uleine–Ellipticine–Vallesamine–Ngouniensine Structural Types |
3.5. |
The Cinchona Structural Type |
3.6. |
The Camptothecin Structural Type |
3.7. |
Terpene, Sesquiterpene, Diterpene and Steroidal Alkaloids (→ ((anchor interlink a26_205.xml Terpenes))) |
3.7.1. |
Overview of Terpenoid Biosynthesis |
3.7.2. |
Monoterpene Alkaloids |
3.7.3. |
Sesquiterpene Alkaloids |
3.7.4. |
Diterpene Alkaloids |
3.7.5. |
Sesterterpene and Triterpene Alkaloids |
3.7.6. |
Steroidal Alkaloids |
4. |
Summary |
References
- 1 K. Yonekura-Sakakibara, K. Saito, Nat. Prod. Rep. 26 (2009) 1466.
- 2 T. Reynolds, Phytochem. 66 (2005) 1399.
- 3 E. Leete, J. Am. Chem. Soc. 85 (1963) 3523.
- 4 B.A. Pfeifer, S.J. Admiraal, H. Gramajo, D.E. Cane, C. Khosla, Science 291 (2001) 1790.
- 5 M.F. Roberts, Phytochemistry 10 (1971) 3057.
- 6 M.F. Roberts, Phytochemistry 16 (1977) 1381.
- 7 M.J. Munchhof, A.I. Meyers, J. Org. Chem. 60 (1995) 1995.
- 8 S. Leclerca, J.C. Braekmann, D. Daloze, Naturwissenschaften 83 (1996) 222.
- 9 J.G. MacConnell, M.S. Blum, H.M. Fales, Tetrahedron 26 (1971) 1129.
- 10 M. MacDonald, New Scientist 189 (2006) 50.
- 11 H.M.T.B. Herath, N.P.D. Nanayakkara, J. Heterocyclic Chem. 45 (2008) 129.
- 12 W. Oppolzer, C.G. Bochet, E. Merifield, Tetrahedron Lett. 35 (1994) 7015.
- 13 A. Reycher, Bull. Soc. Chim. Fr. 19 (1898) 120.
- 14 B. Tursch, D. Daloze, J.C. Braekman, C. Hootele, J.M. Pasteeels, Tetrahedron 31 (1975) 1541.
- 15 D. Daloze, J.-C. Braekman, J.M. Pasteels, Chemoecology 5/6 (1994/1995) 173.
- 16 W.A. Ayer, L.M. Browne, Heterocycles 7 (1977) 685.
- 17 T.R. Gregory, O. Nedved, S.J. Adamowicz, Hereditas 139 (2003) 121.
- 18 A.F. Newton, M. Rejzek, M.-L. Alcaraz, R.A. Stockman: Beilstein J. Org. Chem. 4 (2008) 4.
- 19 A. Méjean, S. Mann, T. Maldiney, G. Vassiliads, O. Lequin, O. Ploux, J. Am. Chem. Soc. 131 (2009) 7512.
- 20 T. Tomita, Y. Kita, T. Kitamura, Y. Sato, M. Mori, Tetrahedron 62 (2006) 10518.
- 21 S. Wonnacott, K.L. Swanson, E.X. Albuquerque, N.J.S. Huby, P. Thompson, T. Gallagher, Biochem. Pharmacol. 43, 1992, 419.
- 22 G. Bringmann, S. Harmsen, J. Holenz, T. Geuder, R. Götz, P. Keller, R. Walter, Y.F. Hallock, J.H. Cardellina, M.R. Boyd, Tetrahedron 50 (1994) 9643.
- 23 T.R. Kelly, A. Garcia, F. Lang, J.J. Walsh, K.V. Bhaskar, M.R. Boyd, R. Götz, P.A. Keller, R. Walter, G. Bringmann, Tetrahedron Lett. 35 (1994) 7621.
- 24 C. Schmitz-Linneweber, R. Regel, T.G. Du, H. Jupfer, R.G. Herrmann, R.M. Maier, Mol. Biol. Evol. 19 (2002) 1602.
- 25 T.J. Barkman, T.R. Martins, E. Sutton, J.T. Stout, Mol. Biol. Evol. 24 (2007) 1320.
- 26 J. Ziegler, P.J. Facchini, Ann. Rev. Plant Biol. 59 (2008) 735.
- 27 N. Hibi, S. Higashiguchi, T. Hashimoto, Y. Yamada, Plant Cell 6 (1994) 723.
- 28 N. Hibi, T. Fujita, M. Hatano, T. Hashimoto, Y. Yamada, Plant Physiol. 100 (1992) 826.
- 29 K.-I. Suzuki, Y. Yamada, T. Hashimoto, Plant Cell Physiol. 40 (1999) 289.
- 30 O. Stenzel, M. Teuber, B. Dräger, Planta 233 (2006) 200.
- 31 A. Katoh, T. Shoji, T. Hashimoto, Plant Cell Physiol. 48 (2007) 550.
- 32 R. Li, D.W. Reed, E. Liu, J. Nowak, L.E. Pelcher, J.E. Page, P.S. Covello, Chem.Bio. 13 (2006) 513.
- 33 S. Gómez-Galera, A.M. Pelacho, A. Gené, P. Cristou, Plant Cell Rep. 26 (2007) 1689.
- 34 E. Leete, J.A. Bojrklund, J.M.M. Couladis, S.H. Kim, J. Am. Chem. Soc. 113 (1991) 9286.
- 35 R. Willstätter, Chem. Ber. 31 (1898) 1534.
- 36 R. Willstätter, Liebig's Ann. 317 (1901) 204.
- 37
R. Willstätter,
Liebig's Ann.
317
(1901)
267.
10.1002/jlac.19013170302 Google Scholar
- 38 R. Willstätter, Liebig's Ann. 317 (1901) 307.
- 39 R. Willstätter, Liebig's Ann. 326 (1903) 1.
- 40 R. Willstätter, Liebig's Ann. 326 (1903) 23.
- 41 R.J. Robinson, Chem. Soc. Trans. 111 (1917) 762.
- 42 A.J. Humphrey, D. O'Hagan, Nat. Prod. Rep. 18 (2001) 494.
- 43 T. Hemscheidt, Topics in Current Chem. 209 (2000) 175.
- 44 D.J.N. Hind, C. Jeffrey, G.V. Pope (eds.): Advances in Compositae systematics, Royal Bot. Gardens, Kew, England, 1995.
- 45 P.R. Cheeke, M.L. Pierson-Goeger, Toxicology Lett. 18 (1983) 343.
- 46 P.P. Fu, Q. Xia, G. Lin, M.W. Chou, Drug Metab. Rev. 36 (2004) 1.
- 47 D. Ober, E. Kaltenegger, Phytochem. 70 (2009) 1687.
- 48 E.C. Wolff, J. Wolff, M.H. Park, J. Biol. Chem. 275 (2000) 9170.
- 49 P.J. Facchini in G.A. Cordell (ed.): The Alkaloids, vol. 63, Elsevier, New York 2006.
- 50 T.A. Geissman, A.C. Waiss, Jr., J. Org. Chem. 27 (1962) 139.
- 51 T. Hashimoto, Y. Yamada, Ann. Rev. Plant Physiol. Plant Mol. Biol. 45 (1994) 257.
- 52 L.H. Nugroho, R. Verpoort, Plant Cell Tissue Org. 68 (2002) 105.
- 53 A. Goossens, H. Rischer, Phytochem. Rev., 6 (2007) 35.
- 54 S.T. Häkkinen, S. Tilleman, A. Šwiatek, V. De Sutter, H. Rischer, I. Vanhoutte, H.V. Onckelen, P. Hilson, D. Inzé, K.-M. Oksman-Caldentey, A. Goossens, Phytochem. 68 (2007) 2773.
- 55
J.B. Friesen,
E. Leete,
Tetrahedron Lett.
34
(1990)
6295.
10.1016/S0040-4039(00)97046-1 Google Scholar
- 56 P. Bieganowski, C. Brenner, Cell 117 (2004) 495.
- 57 G. Noctor, G. Oueval, B. Gakière, J. Exper. Botany 57 (2006) 1603.
- 58 C. Welter, R.M. Moreano, S. Streif, G. Helmchen, Org. Biomol. Chem. 3 (2005) 3266.
- 59 U.S. Dept. of Health and Human Services, NIOSH 97-140, 1997, p. 224.
- 60 T.T. Denton, X. Zhang, J.R. Cashman, Biochem. Pharmacology 67 (2004) 751.
- 61 R.N. Gupta, I.D. Spenser, J. Biol. Chem. 244 (1969) 88.
- 62 E. Leete, Chem. Comm. (1975) 9.
- 63
N.J. Walton,
N.J. Belshaw,
Plant Cell Rep.
7
(1981)
115.
10.1007/BF00270118 Google Scholar
- 64 A. Watson, A.M. Brown, I.J. Colquhoun, N.H. Walton, D.J. Robins, J. Chem. Soc Perkin I, 1990, 2607.
- 65 P.M. Dewick: Medicinal Natural Products, Wiley, New York 1998.
- 66 T. Yi-Shan, L. Ka-Wo, H. Jau-Ling, L. Yu-Sen, J. Suh-Hang, K. Wen-Rei, C. Jan-Gowth, L. Chang-Shen, J. Yuh-Jyh, Toxicology 249 (2008) 230.
- 67 W.M. Golebiewski, I.D. Spenser, Can. J. Chem. 66 (1988) 1734.
- 68 M. Wink, T. Hartmann, Plant Physiol. 70 (1982) 74.
- 69 M.E. Flores-Soto, J. Banuelos-Pineda, S. Orozco-Suarez, R. Schliebs, C. Beas-Zarate, Int. J. Develop. Neurosci. 24 (2006) 401.
- 70 D.S. Patterson, J. Appl. Toxicol. 7 (1987) 51.
- 71 J. Banuelos Pineda, G. Nolasco Rodriguez, J.A. Monteon, P.M. Garcia Lopez, M.A. Ruiz Lopez, G. Estrada, J. Histology and Histopathology 20 (2005) 1147.
- 72 S.H. Hedges, R.B. Herbert, P.C. Wormald, J. Nat. Prod. 56 (1993) 1259.
- 73 B. Colau, C. Hootelé, Can. J. Chem. 61 (1983) 470.
- 74 A. Rother, M.J. Edwards, Phytochem. 36 (1994) 911.
- 75 M.M. Robison, B.F. Lambert, L. Dorfman, W.G. Pierson, J. Org. Chem. 31 (1966) 3220.
- 76 T. Hemscheidt, I.D. Spenser, J. Am. Chem. Soc. 118 (1996) 1799.
- 77 E. Anet, G.K. Hughes, E. Ritchie, Nature 4168 (1949) 501.
- 78 A. Brachet, O. Munoz, M. Gupta, J.-L. Veuthey, P. Christen, Phytochem. 46 (1997) 1439.
- 79 R.C. Menzies, R. Robinson, J. Chem. Soc (Transactions) 1924, 2163.
- 80 A. Rother, J.M. Bobbitt, A.E. Schwarting, Chem. & Ind. (London) 1962, 654.
- 81 J.H. Kim, H. 't Hart, J.F. Stevens, Phytochem. 41 (1996) 1319.
- 82 J.F. Stevens, H. 't Hart, H. Hendrik, T.M. Malingre, Phytochem. 31 (1992) 3917.
- 83 C. Hootele, F. Halin, S. Thomas, D. Tourwe, Tetrahedron 41 (1985) 5563.
- 84 L.P. Dwoskin, P.A. Crooks, Biochem. Pharmacol. 63 (2002) 89.
- 85 Mayo Foundation, WO 200906 1906 (A2), 2009 (C.B. Eckman, W.C. Lee).
- 86 University of Kentricky Research Foundation, US 5830904, 1998 (P.A. Crooks, L.P. Dwoskin).
- 87 R.N. Gupta, I.D. Spenser, Canadian J. C49 (1971) 384.
- 88 M.M. Robison, A.A. Renzi, W.E. Barrett, Experientia 23 (1967) 513.
- 89 C.S. Rumalla, A.N. Jadhav, T. Smillie, F.R. Fronczek, I.A. Khan, Phytochem. 69 (2008) 1756.
- 90
W.J. Lema,
J.W. Blankenship,
M.H. Malone,
J. Ethnopharma
15
(1986)
16.
10.1016/0378-8741(86)90153-4 Google Scholar
- 91 G. Stork, Pure Appl. Chem. 17 (1968) 383.
- 92 T. Hemscheidt, I.D. Spenser, J. Am. Chem. Soc. 112 (1990) 6360.
- 93 R.B. Herbert, Alkaloids (London) 13 (1983) 1.
- 94 J.F. Stevens, H. Hart, H. Hendriks, T.M. Malingré, Plant Systematics Evolution 185 (1993) 207.
- 95 J.C. Craig, S.Y.C. Lee, S.K. Roy, J. Org. Chem. 43 (1978) 347.
- 96 C.M. Harris, M.J. Schneider, F.S. Ungrmach, J.E. Hill, T.M. Harris, J. Am. Chem. Soc. 110 (1988) 940.
- 97 E.C. Clevenstine, H.P. Broquist, T.M. Harris, Biochemistry 18 (1979) 3658.
- 98 M.P. Sibi, J.W. Christensen, J. Org. Chem. 64 (1999) 6434.
- 99 J.P. Michael, Nat. Prod. Rep. 25 (2008) 139.
- 100 H. Uefuji, Y. Tasumi, M. Morimoto, P. Kaothien-Nahayama, S. Ogita, H. Sano, Plant Mol. Biol. 59 (2003) 221.
- 101 K. Mizuno, A. Okuda, M. Kato, N. Yoneyama, K. Tanaka, H. Ashihara, T. Fujimura, FEBS Lett. 534 (2003) 75.
- 102 I.N. Abreu, N.L. Andreazza, A.C.H.F. Sawaya, M.N. Eberlin, P. Mazzafera, Plant Biol. 9 (2007) 793.
- 103 E. Fattorusso, O. Taglialatela-Scafati, Tetrahedron Lett. 41 (2000) 9917.
- 104 K. Nitta, R.G. Stadelmann, C.H. Eugster, Helv. Chim. Acta 60 (1977) 1747.
- 105 A. Cahours, Quat. J. Chem. Soc. 6 (1854) 175.
- 106 J.S. Pruthi: Quality Assurance in Spices and Spice Products, Allied Publishers, New Delhi, India, 1998.
- 107 I.M. Scott, H.R. Jensen, B.J.R. Philogène, J.T. Arnason, Phytochem. Rev. 7 (2008) 65.
- 108 S.-E. Lee, J. Am. Mosquito Control Assoc. 16 (2000) 245.
- 109 T. Suzuki, K. Iwai in A. Brossi (ed.): The Alkaloids, vol. 27, 1944, Academic Press, New York 1944, p. 228ff.
- 110 B.T. Sagdullaev, S.F. Aripova, Chem. Nat. Compounds 36 (2000) 227.
- 111 A.A. Morollo, M.J. Eck, Nat. Struct. Biol. 8 (2001) 234.
- 112 J. Lewis, K.A. Johnson, K.S. Anderson, Biochem. 38 (1999) 7372.
- 113 D.R. Mehta, J.S. Naravane, R.M. Desai, J.Org.Chem. 28 (1963) 445.
- 114 N.J. Leonard, M.J. Martell Jr., Tetrahedron Lett. 25 (1960) 44.
- 115 S.R. Johns, J.A. Lamberton, Aust. J. Chem. 19 (1966) 1991.
- 116 R.M. Bowman, R.M. Grundon, J. Chem. Soc. (C) 1966, 1504.
- 117
Y. Asahina,
T. Ohta,
M. Inubuse,
Ber. Dtsch. Chem. Ges.
63
(1930)
2045.
10.1002/cber.19300630829 Google Scholar
- 118 B. Wolters, U. Eilert, Planta Med. 43 (1981) 166.
- 119 N.S. Narasimhan, R.S. Mali, Tetrahedron 30 (1974) 4153.
- 120 B. Wolters, U. Eilert, Planta Med. 43 (1981) 166.
- 121 J. Reisch, A. Wickramasinghe, W. Probst, Monatsh. Chem. 121 (1990) 829.
- 122 G.K. Hughes, F.N. Lahey, J.R. Price, L.J. Webb, Nature (London) 162 (1948) 223.
- 123 P. Tan, N. Auersperg, Cancer Res. 33 (1973) 2320.
- 124 J. Hlubucek, E. Ritchie, W.C. Taylor, Aust. J. Chem. 23 (1970) 1881.
- 125 J.R. Price, Aust. J. Sci. Res., Ser. A 2 (1949) 249–254.
- 126 G.V. Louie, M.E. Bowman, M.C. Moffitt, T.J. Baiga, B.S. Moore, J.P. Noel, Chem. Biol. 13 (2006) 1327.
- 127 Y.V. Inyushkina, K.V. Kisselv, V.P. Bulgakov, Yu. N. Zhuravlev, Biochemistry (Moscow) 74 (2009) 917.
- 128 Y. Li, X. Li, Y. Jiang, R. Wang, B. Xia, Zeit. Natur. C J. Bio. Sci. 64 (2009) 138.
- 129
D. Havkin-Frenkel,
F.C. Belanger in
R. Verpoorte,
A.W. Alfermann,
T.S. Johnson (eds.):
Applications of Plant Metabolic Engineering,
Springer,
Dordrecht
2007,
p. 175ff.
10.1007/978-1-4020-6031-1_7 Google Scholar
- 130 L. Heide, H. Floss, M. Tabata, Phytochem. 28 (1989) 2643.
- 131 H. Rosenberg, K.L. Khanna, M. Takido, A.G. Paul, Lloydia 32 (1969) 334.
- 132 A. Heffter, Ber. Dtsch. Chem. Ges. 29 (1896) 216.
- 133 C. Van Peteghem, A. Heyndrickx, W. Van Zele, Eur. J. Drug Metab. Pharmacokinet. 7 (1982) 1.
- 134 K. Bahnholzer, T.W. Campbell, H. Schmid, Helv. Chim. Acta 35 (1952) 1577.
- 135 D. Dalton: The Alkaloids, Marcel Dekker, New York 1979, p. 183ff.
- 136 G.J. Kapadia, G.S. Ral, E. Leete, M.G.E. Fayze, Y.N. Naishnav, H.M. Fales, J. Am. Chem. Soc. 92 (1970) 6943.
- 137
A Heffler,
Ber. Dtsch. Chem. Ges.
34
(1901)
3004.
10.1002/cber.190103402266 Google Scholar
- 138 E. Leete, J.D. Braunstein, Tetrahedron Lett. 1969, 451.
- 139 E. Späth, F. Becke, Ber. Dtsch. Chem. Ges. 67 (1934) 2100.
- 140 C. Djerassi, C.R. Smith, S.P. Marfey, R.N. McDonald, A.J. Lemin, S.K. Figdor, H. Estrada, J. Am. Chem. Soc. 76 (1954) 3215.
- 141
E. Späth,
Monatsh. Chem.
42
(1921)
3215.
10.1007/BF01774466 Google Scholar
- 142 A.R. Battersby, T.P. Edwards, J. Chem. Soc. 1960, 1214.
- 143
E. Späth,
F. Becke,
Ber. Dtsch. Chem. Ges.
68
(1935)
501.
10.1002/cber.19350680324 Google Scholar
- 144 M. Naoi, W. Maruyama, G.M. Nagy, Neurotox. 25 (2004) 193.
- 145 R.M. Riggin, M.J. McCarthy, P.T. Kissinger, J. Agric. Food Chem. 24 (1976) 189.
- 146 S. Teitel, J. O'Brien, A. Brossi, J. Med. Chem. 15 (1972) 845.
- 147 T. Nomura, A.L. Quesada, T.M. Kutchan, J. Biological Chem. 238 (2008) 34650.
- 148 A. Itoh, Y. Baba, T. Tanahashi, N. Nagakura, Phytochem. 59 (2002) 91.
- 149 A.R. Battersby, G.C. Davidson, B.J.T. Harper, J. Chem. Soc. 1959, 1744.
- 150 H.T. Openshaw, N. Whittaker, J. Chem. Soc. 1963, 1461.
- 151 A.R. Cushny: Textbook of Pharmacology and Therapeutics, Lea and Febiger, New York 1918, pp. 438ff.
- 152 Y.-D. Zhou, Y.-P. Kim, K.A. Mohammed, D.K. Jones, I. Muhammad, D.C. Dunbar, D.G. Nagle, J. Nat. Prod. 68 (2005) 947.
- 153 J.D. Albright, J.C. Van Meter, L. Goldman, Lloydia 28 (1965) 212.
- 154 C. Szántay, L. Töke, P. Kolonits, J. Org. Chem. 31 (1966) 447.
- 155 P. Bellet, Ann. Pharma. Fr. 12 (1954) 466.
- 156 A.R. Battersby, B. Gregory, H. Spencer, J.C. Turner, M.-M. Janot, P. Potier, P. Francois, J. Levisalles, Chem. Comm. 1967, 219.
- 157 A.R. Battersby, A.R. Burnett, P.G. Parsons, J. Chem.Soc. (C) 1969, 1187.
- 158 M.J. Gasson, Y. Kitamura, W.R. McLauchlan, A. Narbad, A.J. Parr, E.L.H. Parsons, J. Payne, M.J.C. Rhodes, N.J. Walton, J. Biol. Chem. 237 (1998) 4168.
- 159 P.M. Leonard, C.M. Marshall, E.J. Dodson, N.J. Walton, G. Grogan, Acta Cryst. D60 (2004) 2343.
- 160 D.H.R. Barton, T. Cohen: Festschrift Arthur Stoll, Birkhäuser Verlag, Basel 1957, pp. 117–143.
- 161 Z. Jin, Nat. Prod. Rep. 22 (2005) 111.
- 162 I.D. Spenser in M. Florkin, E.H. Stotz (eds.): Comprehensive Biochemistry, vol. 20, Elsevier, New York 1968. pp. 231–413.
- 163 A. Brossi, G. Grethe, S. Teitel, W.C. Wildman, D.T. Bailey, J. Org. Chem. 36 (1970) 1100.
- 164 A. Brossi, S. Teitel, J. Org. Chem. 35 (1970) 3559.
- 165 S. Lebrun, Org. Biomolec. Chem. 1 (2003) 1701.
- 166 K. Leander, B. Lüning, E. Ruusa, Acta Chem. Scand. 23 (1969) 244.
- 167 S.F. Martin: The Alkaloids, Academic Press, vol. 30, New York 1987, p. 251ff.
- 168 S. Takagi, W.I. Taylor, S. Uyeo, H. Yajima, J. Chem. Soc. 1955, 4003.
- 169 R.K. Boeckman, S.W. Goldstein, M.A. Walters, J. Am. Chem. Soc. 110 (1988) 8250.
- 170 H.M. Fales, W.C. Wildman, J. Am. Chem. Soc. 80 (1958) 4395.
- 171 T. Kitagawa, S. Uyeo, N. Yokoyama, J. Chem. Soc. 1955, 1066.
- 172 J. Renz, D. Stauffacher, E. Seebeck, Helv. Chim. Acta 38 (1955) 1209.
- 173 F. Sandberg, K.H. Michel, Lloydia 26 (1963) 78.
- 174 M.A. Schwartz, R.A. Holton, J. Am. Chem. Soc. 92 (1970) 1090.
- 175 L.H. Mason, E.R. Puschett, W.C. Wildman, J. Amer. Chem. Soc. 77 (1955) 1253.
- 176 W.C. Wildman, H.M. Fales, J. Amer. Chem. Soc. 80 (1958) 6465.
- 177 H.M. Fales, W.C. Wildman, J. Amer. Chem. Soc. 82 (1960) 197.
- 178 Y. Tsuda, K. Isobe, Chem. Comm. 1971, 1555.
- 179 H.-G. Boit, H. Ehmke, Chem. Ber. 89 (1956) 2093.
- 180 J.B. Hendrickson, T.L. Bogard, M.E. Fisch, S. Grossert, N. Yoshimura, J. Am. Chem. Soc. 96 (1974) 7781.
- 181 P. Magnus, J. Sane, B.P. Fauber, V. Lynch, J. Am. Chem. Soc. 131 (2009) 16047.
- 182 A.-W. Hong, T.-H. Cheng, V. Raghukumar, C.-K. Sha, J. Org. Chem. 73 (2008) 7580.
- 183 T. Hudlický, J.W. Reed: The Way of Synthesis, Wiley-VCH, Weinheim 2007.
- 184 P. Forgo, J. Hohmann, J. Nat. Prod. 68 (2005) 1588.
- 185 S. Kobayashi, M. Kihara, K. Yuasa, Y. Imakura, T. Shingu, A. Kato, T. Hashimoto, Chem. Pharm. Bull. (Japan) 33 (1985) 5258.
- 186 S.Y. Han, J.E. Sweeney, E.S. Bachman, E.J. Schweiger, G. Forloni, J.T. Coyle, B.M. Davis, M.M. Joullie, Eur. J. Med. Chem. 27 (1992) 673.
- 187 M. Kihara, T. Koike, Y. Imakura, K. Kida, T. Shingu, S. Kobayashi, Chem. Pharm. Bull (Japan) 35 (1987) 1070.
- 188 H.-G. Boit, W. Döpke, A. Beitner, Chem. Ber. 90 (1957) 2197.
- 189 W.-C. Shieh, J.A. Carlson, J. Org. Chem. 59 (1994) 5463.
- 190
M. Node,
S. Kodama,
Y. Hamashima,
T. Baba,
N. Hamamichi,
K. Nishide,
Angew. Chem., Int. Ed.
40
(2001)
3060.
10.1002/1521-3773(20010817)40:16<3060::AID-ANIE3060>3.0.CO;2-# CAS PubMed Web of Science® Google Scholar
- 191 M. Ochi, H. Otsuki, K. Nagao, Bull. Chem. Soc. Jpn. 49 (1976) 3363.
- 192 W.C. Wildman, C.L. Brown, J. Am. Chem. Soc. 90 (1968) 6439.
- 193 L.H. Briggs, L.D. Colebrook, H.M. Fales, W.C. Wildman, Anal. Chem. 29 (1957) 904.
- 194 Y. Inubushi, H.M. Fales, E.W. Warnhoff, W.C. Wildman, J. Org. Chem. 25 (1960) 2153.
- 195 R.C. Clark, F.L. Warren, K.G.R. Pachler, Tetrahedron 31 (1975) 1855.
- 196 J. Jin, S.M. Weinreb, J. Am. Chem. Soc. 119 (1997) 5773.
- 197 L.J. Dry, M. Poynton, M.E. Thompson, F.L. Warren, J. Chem. Soc. 1958, 4701.
- 198 G. Grue-Sørensen, I.D. Spenser, J. Am. Chem. Soc. 116 (1994) 6195.
- 199 L. Xiang, B.S. Moore, J. Bacteriology 185 (2003) 399.
- 200 H. Emde, Helv. Chim. Acta 12 (1929) 365.
- 201 G.V. Reddy, G.V. Rao, V. Sreevani, D.S. Iyengar, Tetrahedron Lett. 41 (2000) 953.
- 202 W.J. Close, J. Org. Chem. 15 (1950) 1131.
- 203 F.W. Hoover, H.B. Hass, J. Org. Chem. 12 (1947) 506.
- 204 O. Wolfes, Arch. Pharm. 268 (1930) 81.
- 205
W. Leithe,
Chem. Ber.
65
(1932)
660.
10.1002/cber.19320650432 Google Scholar
- 206 J.J. Maresh, L.-A. Giddings, A. Freidrich, E.A. Loris, S. Panjikar, B.L. Trout, J. Stöckigt, B. Peters, S.E. O'Commor, J. Am. Chem. Soc. 130 (2008) 710.
- 207
T.M. Kutchan,
S. Frick,
M. Weid in
H.J. Bohnert,
H. Nguyen,
N.G. Lewis (eds.):
Bioengineering and Molecular Biology of Plant Pathways, vol. 1,
Elsevier,
New York
2008,
p. 283ff.
10.1016/S1755-0408(07)01010-7 Google Scholar
- 208 Y.-C. Chang, F.-R. Chang, A.T. Khalil, P.-W. Hsieh, Y.-C. Wu, Zeitschrift Naturforschung, C: J. of Biosci. 58 (2003) 521.
- 209 N. Masaki, H. Iizuka, M. Yokota, A. Ochiai, J. Chem. Soc. Perkin 1 1977, 717.
- 210 Y. Kashiwada, A. Aoshima, Y. Ikeshiro, Y.-P. Chen, H. Furukawa, M. Itoigawa, T. Fujioka, K. Mihashi, L.M. Cosentino, S.L. Morris-Natschke, K.-H. Lee, Bioorg. Med. Chem. 13 (2005) 443.
- 211 J. Finkelstein, J. Am. Chem. Soc. 1951, 73.
- 212 D.A. Guthrie, W. Arlen, C.B. Purves, Can. J. Chem. 33 (1955) 729.
- 213 F.D. Popp, W. McEwen, J. Am. Chem. Soc. 79 (1957) 3773.
- 214 P. Tucci, M. Palmery, P. Piccolotti, G. Pimpinella, P. Valeri, L. Romanelli, Neurogastroenter. Motil. 20 (2008) 958.
- 215 D.S. Bhakuni, V.M. Labroo, A.N. Singh, R.S. Kapil, J. Chem. Soc, Perkin 1 1 1978, 1972.
- 216 Q. Xu, M. Lin, J. Nat. Prod. 62 (1999) 102.
- 217 J.R. Boissier, G. Combes, R. Pernet, C. Dumont, Lloydia (J. Nat. Prod.) 28 (1965) 191.
- 218 I.R.C. Bick, P.S. Clezy, J. Chem. Soc. 1953, 3893.
- 219 J.D. Dutcher, J. Am. Chem. Soc. 6 (1946) 419.
- 220 D.A.A. Kidd, J. Walker, J. Chem. Soc. 1954, 669.
- 221 M. Tomita, Y. Inubushi, K. Ito, Pharm. Bull. 2 (1954) 372.
- 222 Y. Chen, J.-C. Chen, S.-H. Tseng, Int. J. Cancer 124 (2009) 2260.
- 223 M. Shamma, W.A. Slusarchyk, Chem. Rev. 64 (1964) 59.
- 224 A.R. Rufino, A.J.C. Brant, J.B.O. Santos, M.J.P. Ferreira, V.P. Emerenciano, J. Chem. Inf. Model. 45 (2005) 645.
- 225 Q.N. Saqib, K. Usmanghani, V.U. Ahmad, J. Pharm., Univ. Karachi 4 (1985) 39.
- 226 S. Frick, R. Kramell, J. Schmidt, A.J. Fist, T.M. Kutchan, J. Nat. Prod. 68 (2005) 666.
- 227 A. Gesell, M. Rolf, J. Ziegler, C. Diaz, L. Maria, F.-C. Huang, T.M. Kutchan, J. Biol. Chem. 284 (2009) 24432.
- 228 E. Brochmann-Hanssen, B. Nielsen, Tetrahedron Lett. (1965) 1271.
- 229 A.R. Battersby, R. Binks, D.M. Foulkes, R.J. Francis, D.J. McCaldin, H. Ramuz, Proc. Chem. Soc. (London) 1963, 203.
- 230 B. Frydman, R. Bendish, V. Deulofeu, Tetrahedron 4 (1958) 342; L.E. Craig, D.S. Tarbell, J. Am. Chem. Soc. 70 (1948) 2783.
- 231 A.R. Battersby, J. Chem. Soc. 1965, 4550.
- 232 T. Kametani, M. Ihara, M. Takemura, Y. Satoh, H. Terasawa, Y. Ohta, K. Fukumoto, K. Takahashi, J. Am. Chem. Soc. 99 (1977) 3805.
- 233 W. Klee, Archiv Pharm (Weinheim) 252 (1914) 211.
- 234 P.S. Clezy, E. Gellert, D.Y.K. Lau, A.W. Nichol, Aust. J. Chem. 19 (1966) 135.
- 235 S.R. Johns, J.A. Lamberton, A.A. Sioumis, Aust. J. Chem. 19 (1966) 2331.
- 236 V.E. Davies, M.J. Walsh, Science 167 (1970) 1005, 1006.
- 237 K.C. Rice, A. Brossi, J. Org. Chem. 45 (1980) 592.
- 238 K. Sango, W. Maruyama, K. Matsubara, P. Dostert, C. Minami, M. Kawai, M. Naoi, Neurosci. Lett. 283 (2000) 224.
- 239 C. Boettcher, M. Fellermeier, C. Boettcher, B. Draeger, M.H. Zenk, PNAS (USA) 102 (2005) 8495.
- 240 S. Ghosal, S.K. Majumdar, A. Chakraborti, Aust J. Chem. 24 (1971) 2733.
- 241 F.R. Stermitz, J.N. Seiber, J. Org. Chem. 31 (1966) 2925.
- 242 M.J. Martell, Jr., T.O. Soine, L.B. Kier, J. Am. Chem. Soc. 85 (1963) 1022.
- 243 D.H.R. Barton, G.W. Kirby, W. Steglich, G.M. Thomas, A.R. Battersby, T.A. Dobson, H. Ramuz, J. Chem. Soc. 1965, 2423.
- 244 D.H.R. Barton, A.J. Kirby, G.W. Kirby, Chem. Comm. 1965, 52.
- 245 T. Kametani, M. Ihara, K. Fukumoto, H.J. Yagi, J. Chem. Soc. (C) 1969, 2030.
- 246 K.W. Bentley: Chemistry of the Morphine Alkaloids, Oxford Univ. Press, Oxford 1954, p. 184.
- 247 N. Grobe, B. Zhang, U. Fisinger, T.M. Kutchan, M.H. Zenk, F.P. Guengerich, J. Biol. Chem. 284 (2009) 24425.
- 248 K. Kempe, Y. Higashi, S. Frick, K. Sabarna, T.M. Kutchan, Phytochem. 70 (2009) 579.
- 249 K.W. Bentley: Chemistry of the Morphine Alkaloids, Oxford Univ. Press, Oxford 1954, p. 107 ff.
- 250 G.J. Grant, K. Vermeulen, M.I. Zakowski, M. Stenner, H. Turndorf, L. Langerman, Anesthesia and Analgesia 79 (1994) 706.
- 251 A.J. Walker, N.C. Bruce, Tetrahedron 60 (2004) 561.
- 252 J. Gollwitzer, R. Lenz, N. Hampp, M.H. Zenk, Tetrahedron Lett. 34 (1993) 5703.
- 253 K.W. Bentley, Chemistry of the Morphine Alkaloids, Oxford University Press, Oxford 1954, p. 57ff.
- 254 S.P. Findlay, L.F. Small, J. Am. Chem. Soc. 72 (1950) 3247.
- 255 D.D. Weller, H. Rapoport, J. Med. Chem. 19 (1976) 1171.
- 256 W.H. Moos, R.D. Gless, H. Rapoport, J. Org. Chem. 48 (1983) 227.
- 257 B. Nielsen, J. Röe, E. Brochmann-Hanssen, Planta Med. 48 (1983) 205.
- 258 A. Coop, J.W. Janetka, J.W. Lewis, K.C. Rice, J. Org. Chem. 63 (1998) 4392.
- 259 H. Rapoport, D.R. Baker, H.N. Reist, J. Org. Chem. 22 (1957) 1489.
- 260 V.O. Nikolaev, C. Boettcher, C. Dees, M. Buenemann, M.J. Lohse, M.H. Zenk, J. Biol. Chem. 282 (2007) 27126.
- 261 T. Todaka, T. Ishida, H. Kita, S. Narimatsu, S. Yamano, Biol. Pharm. Bull. 28 (2005) 1275.
- 262 F. Sunan, A.E. Takemori, P.S. Portoghese, J. Med. Chem. 27 (1984) 1361.
- 263
R.H.F. Manske,
Can. J. Res.
17B
(1939)
57.
10.1139/cjr39b-010 Google Scholar
- 264 S. Frick, R. Kramell, J. Schmidt, A.J. Fist, T.M. Kutchan, J. Nat. Prod. 68 (2005) 666.
- 265 N. Ikezawa, K. Iwasa, F. Sato, FEBS Journal 274 (2007) 1019.
- 266 K. Feist, Archiv Pharm. 245 (1908) 586.
- 267 H. Corrodi, E. Hardegger, Helv. Chim. Acta 39 (1956) 889.
- 268 M.E. Sanchez-Mendoza, C. Castillo-Henkel, A. Navarrete, J. Pharm. Pharmacol. 60 (2008) 229.
- 269 R. Istatkova, S. Philipov, A. Sidjimov, A. Vitkova, S. Andreev, Comptes Rendus de l'Acad. Bulg. Sci. 61 (2008) 81.
- 270 M. Kobayashi, T. Frenzel, J.P. Lee, M.H. Zenk, H.G. Floss, J. Am. Chem. Soc. 109 (1987) 6184.
- 271 V. Rosenkranz, M. Wink, Molecules 13 (2008) 2462.
- 272
V. Deulofeu,
R. Labriola,
J. de Langhe,
J. Am. Chem. Soc.
64
(1942)
2326.
10.1021/ja01262a030 Google Scholar
- 273
R.H.F. Manske,
Can. J. Res.
17B
(1939)
51–56.
10.1139/cjr39b-009 Google Scholar
- 274 R.D. Haworth, W.H. Perkin Jr., J. Chem. Soc. 1926, 445.
- 275 S.G. Pyne, Tetrahedron Lett. 28 (1987) 4737.
- 276 R.H.A. Janssen, P. Wijkens, C. Kruk, H.W.A. Biessels, F. Menichini, H.G. Theuns, Phytochem. 29 (1990) 3331.
- 277 K.M. Hawkins, C. Smolke, Nature Chem. Biol. 4 (2008) 564.
- 278 X.-L. Wang, Z.-X. Lia, G.-W. Qinb, Acta Cryst. E. 62 (2006) 081.
- 279 W. Bauer, M.H. Zenk, Tetrahedron Lett. 30 (1989) 5257.
- 280 J. Slavik, L. Slavikova, Coll. Czech. Chem. Comm. 54 (1989) 2009.
- 281 W. Bauer, M.H. Zenk, Tetrahedron Lett. 32 (1991) 487.
- 282
R.H.F. Manske,
Can. J. Res.
18B
(1940)
288.
10.1139/cjr40b-036 Google Scholar
- 283 Y. Fu, Y. Zhou, X. Liao, B. Bai, S. Peng, L. Ding, Planta Medica 75 (2009) 547.
- 284 I. Orhan, B. Ozcelik, T. Karaoglu, B. Sener, Zeitschrift für Naturforschung, C 62 (2007) 19.
- 285 J.O. Schlotterbeck, H.C. Watkins, J. Am. Chem. Soc. 24 (1902) 1.
- 286 J. Gadamer, Archiv der Pharmazie 249 (1911) 224.
- 287 W.H. Perkin, Jr., J. Chem. Soc. Transactions 109 (1916) 815.
- 288
R.H.F. Manske,
Can. J. Res.
17B
(1939)
399.
10.1139/cjr39b-054 Google Scholar
- 289 M. Tomita, M. Sugamoto, Yakugaku Zasshi 81 (1961) 1090.
- 290 A.S. Bailey, R. Robinson, R.S. Staunton, Nature (London) 165 (1950) 235.
- 291 H. Ahsan, S. Reagan-Shaw, J. Breur, N. Ahmad, Cancer Lett. (Amsterdam) 249 (2007) 198.
- 292
H. Ishii,
K.I. Harada,
T. Ishida,
E. Ueda,
K. Nakajima,
I. Ninomiya,
T. Naito,
T. Kiguchi,
Tetrahedron Lett.
5
(1975)
319.
10.1016/S0040-4039(00)71853-3 Google Scholar
- 293 H. Ishii, T. Ishikawa, J. Pharm. Soc. (Japan) 101 (1981) 663.
- 294 J. Slavik, L. Slavikova, Coll. Czech. Chem. Comm. 20 (1955) 198.
- 295 N. Takao, M. Kamigauchi, M. Okada, Helv. Chim. Acta 66 (1983) 473.
- 296 R. Stadler, T.M. Kutchan, M.H. Zenk, Phytochem. 28 (1989) 1083.
- 297 J. Ziegler, P.J. Facchini, Ann. Rev. Plant Biol. 59 (2008) 738.
- 298 J.-C. Quirion: “Novel Dimeric Indole Alkaloids from Aristotelia australasica. Structural Determination and Synthesis”, Ph.D. Thesis, Université de Paris-Sud, Centre d'Orsay, Paris 1986.
- 299 H.-J. Borschberg in J.E. Saxton (ed.): The Monoterpenoid Indole Alkaloids, suppl. vol., Wiley, New York 1994, Chap. 2.
- 300 M. Dobbler, J.C. Anderson, M. Juch, H.-J. Borschber, Helv. Chim. Acta 78 (1995) 272.
- 301 J.C. Quirion, C. Kan, H.P. Husson, I.R.C. Bick, J. Nat. Prod. 53 (1990) 713.
- 302 R.E. Moore, C. Cheuk, G.M.L. Patterson, J. Am. Chem. Soc. 106 (1984) 6456.
- 303 R.E. Moore et al., J. Org. Chem. 52 (1987) 1036.
- 304 V. Bornemann, G.M.L. Patterson, R.E. Moore, J. Am. Chem. Soc. 110 (1988) 2339.
- 305 H. Kochi, G. Kikuchi, J. Biochem. 75 (1974) 1113.
- 306 H. Fujiki, M. Mori, M. Nakayasu, M. Terada, T. Sugimura, R.E. Moore, Proc. Natl. Acad. Sci. USA, 78 (1981) 3872.
- 307 K. Irie, S. Kajiyama, A. Funaki, K. Koshimizu, Tetrahedron Lett. 31 (1990) 101.
- 308 S. Nakatsuka, T. Masuda, K. Sakai, T. Goto, Tetrahedron Lett. 27 (1986) 5735.
- 309 K. Irie, N. Hagiwara, K. Koshimizu, Tetrahedron Lett. 28 (1987) 3267.
- 310
A.J. Birch,
J.J. Wright,
J. Chem. Soc. D: Chem. Comm.
12
(1969)
644.
10.1039/c2969000644b Google Scholar
- 311 J.M. Schkeryantz, J.C.G. Woo, P. Siliphaivanh, K.M. Depew, S.J. Danishefsky, J. Am. Chem. Soc. 121 (1999) 11964.
- 312 T. Kametani, N. Kanaya, M. Ihara, J. Am. Chem. Soc. 102 (1980) 3974.
- 313 J.F. Sanz-Cervera, T. Glinka, R.M. Williams, Tetrahedron 49 (1993) 8471.
- 314 A. Stoll, A. Hofmann, Z. Physiol. Chem. 250 (1937) 7.
- 315 A. Hofmann, Farmacognosia 13 (1953) 311.
- 316 A. Stoll, A. Hofmann, B. Becker, Helv. Chim. Acta 26 (1943) 1602.
- 317 W. Schlientz, R. Brunner, P.A. Stadler, A.J. Frei, H. Ott, A. Hofmann, Helv. Chim. Acta 47 (1964) 1921.
- 318 E.C. Kornfeld, G.B. Kline, E.J. Fornefeld, US 2796419, 1957.
- 319 E.C. Kornfeld, G.B. Kline, E.J. Fornefeld, US 19570618, 1957.
- 320 D. Groeger, D. Erge, H.G. Floss, Z. Naturforschung B21 (1966) 27.
- 321 T. Kiguchi, C. Hashimoto, I. Ninomiya, Heterocycles 22 (1984) 43.
- 322
T.-C. Choong,
H.R. Shough,
Tetrahedron Lett.
36
(1977)
3137.
10.1016/S0040-4039(01)83180-4 Google Scholar
- 323 A. Hofmann, R. Brunner, H. Kobel, A. Brack, Helv. Chim. Acta 40 (1957) 1358.
- 324 M. Natsume, H. Muratake, Heterocycles 16 (1981) 375.
- 325 D. Stauffacher, N. Tscherter, Helv. Chim. Acta 47 (1964) 2186.
- 326 Th. Fehr, W. Acklin, D. Arigoni, Chem. Comm. (London) 21 (1966) 801.
- 327 A. Stoll, A. Hofmann, Helv. Chim. Acta 33 (1950) 1705.
- 328 M. Ram, K.L. Handa, Indian J. Chem. 3 (1965) 42.
- 329 C. Galeffi, S. Matosic, A. Tonolo, Matematiche e Naturali, Rendiconti 56 (1974) 951.
- 330 T. Haarmann, N. Lorenz, P. Tudzynski, Fungal Gen Bio 45 (2008) 35.
- 331 A. Hofmann, H. Ott, R. Griot, P.A. Stadler, A.J. Frey, Helv. Chim. Acta 46 (1963) 2506.
- 332 A. Stoll, E. Burckhardt, Z. Physiol. Chem. 250 (1937) 1.
- 333 P.A. Stadler, S. Guttmann, H. Hauth, R.L. Huguenin, E. Sandrin, G. Wersin, H. Willems, A. Hofmann, Helv. Chim. Acta 52 (1969) 1549.
- 334 J.-M. Chao, A.H. DerMarderosian, Phytochem. 12 (1973) 2435.
- 335 P.A. Stadler, A.J. Frey, H. Ott, A. Hoffmann, Helv. Chim. Acta 47 (1964) 1911.
- 336 B. Falkewicz, J. Lukasiak, Case Rep. Clin. Pract. Rev. 2 (2001) 305.
- 337 M. Shimizu, F. Uchimaru, Chem. Pharm. Bull. (Japan) 7 (1959) 713.
- 338 A. Hofmann, Helv. Chim. Acta 37 (1954) 849.
- 339 J.F. Kreimer, M.H. Zenk, Phytochem. 17 (1978) 227.
- 340 H. King, J. Chem. Soc. 1949, 3263.
- 341 J. Haginiwa, S. Sakai, N. Aimi, E. Yamanaka, N. Shinma, Yakugaku Zasshi 93 (1973) 448 (CA required).
- 342 M.M. Janot, R. Goutarel, Bull. Soc. Chim. Fr. 1951, 588.
- 343 E.J. Shellard, A.H. Beckett, P. Tantivatana, J.D. Phillipson, C.M. Lee, J. Pharm. Pharmacol. 17 (1965) 753.
- 344K. Konno,
H. Inoue,
M. Fujiwara, et al.,
Antiviral Res.
34
(1997)
88.
10.1016/S0166-3542(97)83306-2 Google Scholar
- 345 H. Takayama, Y. Iimura, M. Kitajima, et al., Bioorg. Med. Chem. Lett. 7 (1997) 3145.
- 346 H. Masumiya, T. Saitoh, Y. Tanaka, et al., Life Sci. 65 (1999) 2333.
- 347 Y. Shimada, H. Goto, T. Itoh, et al., J. Pharm. Pharmacol. 51 (1999) 715.
- 348 E.J. Shellard, P. Tantivatana, A.H. Beckett, Planta Medica 15 (1967) 366.
- 349 E. Grenadier, G. Alpan, D. Weiss, A. Marmor, A. Palant, Angiology 34 (1983) 204.
- 350 G. Iacobucci, V. Deulofeu, J. Org. Chem. 22 (1957) 94.
- 351 T.-H. Kang, Y. Murakami, K. Matsumoto, H. Takayama, M. Kitajima, N. Aimi, H. Watanabe, Eur. J. Pharmacol. 455 (2002) 27.
- 352 H. Kondo, T. Fukuda, M. Tomita, Yakugaku Zasshi 48 (1928) 321.
- 353 J.D. Phillipson, S.R. Hemingway, Phytochem. 13 (1974) 2621.
- 354 C.L. Cardoso, I. Castro-Gamboa, D.H.S. Silva, M. Furlan, R.D.A. Epifanio, A.C. Pinto, C.M. Rezende, J.A. Lima, V. de S. Bolzani, J. Nat. Prod. 67 (2004) 1882.
- 355 C.L. Cardoso, D.H.S. Silva, D.M. Tomazela, H. Verli, M.C.M. Young, M. Furlan, M.N. Eberlin, V. de S. Bolzani, J. Nat. Prod. 66 (2003) 1017.
- 356 C. Szántay, K. Honty in J.E. Saxton (ed.): The Monoterpenoid Indole Alkaloids, suppl. vol., John Wiley & Sons, Chichester 1994, pp. 163ff.
- 357 A.-U. Rahman, A. Basha: Indole Alkaloids, Overseas Publishers Association, Amsterdam 1998, Chap. 94, pp. 309ff.
- 358 A. Itoh, T. Kumashiro, M. Yamaguchi, N. Nagakura, Y. Mizushina, T. Nishi, T. Tanahashi, J. Nat. Prod. 68 (2005) 848.
- 359 S.M. Tam, M. Worcel, M. Wyllie, Pharmacology & Therapeutics 91 (2001) 215.
- 360 C. Szántay, K. Honty in J.E. Saxton (ed.): The Monoterpenoid Indole Alkaloids, suppl.vol., John Wiley & Sons, Chichester 1994, pp. 173 ff.
- 361 C. Djerassi, M. Gorman, A.L. Nussbaum, J. Reynoso, J. Am. Chem. Soc. 76 (1954) 4463.
- 362 H.S. Fraser, Clinical Pharmacology and Therapeutics (St. Louis) 60 (1996) 368.
- 363 R.B. Woodward, F.E. Bader, H. Bickel, A.J. Frey, R.W. Kierstead, J. Am. Chem. Soc. 78 (1956) 2023.
- 364 J.R.W. Menzies, S.J. Paterson, M. Duwiejua, A.D. Corbett, Eur. J. Pharmacol. 350 (1998) 101.
- 365 P.V.V. Srirama-Sarma, J.M. Cook, Org. Lett. 8 (2006) 1017.
- 366 S. Silvers, A. Tulinsky, Tetrahedron Lett. (1962) 339.
- 367 J. Levy, J. Le Men, M.M. Janot, Compt. Rend. Acad. Sci. 253 (1961) 131.
- 368 M. Gorman, N. Neuss, C. Djerassi, J.P. Kutney, P.J. Scheuer, Tetrahedron 1 (1957) 328.
- 369 M.-L. Bennasar, B. Vidal, J. Bosch, J. Org. Chem. 62 (1997) 3597.
- 370 W.G. Earley, J.E. Jacobsen, A. Madin, G.P. Meier, C.J. O'Donnell, T. Oh, D.W. Old, L.E. Overman, M.J. Sharp, J. Am. Chem. Soc. 127 (2005) 18054.
- 371 P. Magnus, B. Mugrage, M. DeLuca, G.A. Cain, J. Am. Chem. Soc. 111 (1989) 786.
- 372 S.F. Martin, C.W. Clark, M. Ito, M. Mortimore, J. Am. Chem. Soc. 118 (1996) 9804.
- 373 J.A. Joule, M. Okashi, B. Gilbert, C. Djerassi, Tetrahedron 21 (1965) 1717.
- 374 I.K. Kim, K.L. Erickson, Tetrahedron 27 (1971) 3979.
- 375 C.H. Baggio, G.D.M. Otofuji, W.M. de Souza, C.A. de M. Santos, L.M.B. Torres, L. Rieck, M.C. de A. Marques, S. Mesia-Vela, Planta Med. 71 (2005) 733.
- 376 M. Saito, M. Kawamura, K. Hiroya, K. Ogasawara, Chem. Commun. 1997, 765.
- 377 J. Schmutz, F. Hunziker, R. Hirt, Helv. Chim. Acta 40 (1957) 1189.
- 378 S. Goodwin, A.F. Smith, E.C. Horning, J. Am. Chem. Soc. 1959, 1903.
- 379 R.B. Woodward, G.A. Iacobucci, F.A. Hochstein, J. Am. Chem. Soc. 1959, 4434.
- 380 J. Poljakova, E. Frei, J.E. Gomez, D. Aimova, T. Eckschlager, J. Hrabeta, M. Stiborova, Cancer Lett. 252 (2007) 270.
- 381 M. Sainsbury, B. Webb, R. Schinazi, J. Chem. Soc. Perkin 1 3 (1975) 289.
- 382 M. Alvarez, J.A. Joule in J.E. Saxton (ed.): The Monoterpenoid Indole Alkaloids, suppl. vol., John Wiley & Sons, Chichester 1994, pp. 272.
- 383 A.I. Atta-ur-Rahman, K.A. Alvi, S.A. Abbas, W. Voelter, Heterocycles 26 (1987) 413.
- 384 T. Yamauchi, F. Abe, R. Chen, G. Nonaka, T. Santisuk, W.G. Padolina, Phytochemistry 29 (1990) 3547.
- 385 A. Walser, C. Djerassi, Helv. Chim. Acta 47 (1964) 2072.
- 386 J.A. Joule, H. Monteiro, L.J. Durham, B. Gilbert, C. Djerassi, J. Chem. Soc. 1965, 4773.
- 387 W. Pratchayasakul, A. Pongchaidecha, N. Chattipakorn, S. Chattipakorn, Indian J. Med. Res. 127 (2008) 317.
- 388 M.-L. Bennasar, E. Zulaica, D. Sole, S. Alonso, Chem. Commun. 2009, 3372.
- 389 G. Massiot, M. Zèches, P. Thépenier, M.-J. Jacquier, L. Le Men-Olivier, C. Delaude, J. Chem. Soc., Chem. Commun. 1982, 768.
- 390 M. Alvarez, J.A. Joule in J.E. Saxton (ed.): The Monoterpenoid Indole Alkaloids, suppl. vol., John Wiley & Sons, Chichester 1994, Chap. 6, pp. 275.
- 391 A.I. Scott, C.C. Wei, J. Am. Chem. Soc. 94 (1972) 8263.
- 392 D. Passarella, M. Martinelli, N. Llor, M. Amat, J. Bosch, Tetrahedron 55 (1999) 14995.
- 393 M. Frédérich, M.-J. Jacquier, P. Thépenier, P. De Mol, M. Tits, G. Philippe, C. Delaude, L. Angenot, M. Zèches-Hanrot, J. Nat. Prod. 65 (2002) 1381.
- 394 J. Bosch, M.-L. Bennasar, E. Zulaica, G. Massiot, B. Massoussa, Tetrahedron Lett. 28 (1987) 231.
- 395 J.B. Hendrickson in R.H.F. Manske (ed.): The Alkaloids, vol. 6, Academic Press, New York 1960, pp. 179ff and references therein.
- 396 P.J. Pelletier, J.B. Caventou, Ann. Chim. Phys. 8 (1818) 323.
- 397 P.J. Pelletier, J.B. Caventou, Ann, Chim. Phys. 10 (1819) 142.
- 398 A.F. Peerdeman, Acta Cryst. 9 (1956) 824.
- 399 R.B. Woodward, M.P. Cava, W.D. Ollis, A. Hunger, H.U. Daeniker, K. Schenker, Tetrahedron 19 (1963) 247.
- 400 P.J. Pelletier, J.B. Caventou, Ann. Chim. Phys. 12 (1820) 113.
- 401 S.G. Glover, Acta Crystallogr. C41 (1985) 990.
- 402 E. Tedeschi, S. Dukler, P. Pfeffer, D. Lavie, Tetrahedron 24 (1968) 4573.
- 403 H. Wieland, W. Gumlich, Annalen 494 (1932) 191.
- 404 H. Asmis, H. Schmid, P. Karrer, Helv. Chim. Acta 37 (1954) 1968.
- 405 P. Magnus, M. Giles, R. Bonnert, G. Johnson, L. McQuire, M. Deluca, A. Merritt, C.S. Kim, N. Vicker, J. Am. Chem. Soc. 115 (1993) 8116.
- 406 D. Stauffacher, Helv. Chim. Acta 44 (1961) 2006.
- 407 A. Sandoval, F. Walls, J.N. Shoolery, J.M. Wilson, H. Budzikiewiez, C. Djerassi, Tetrahedron Lett. (1962) 409.
- 408 K. Biemann, A.L. Burlingame, D. Stauffacher, Tetrahedron Lett. (1962) 527.
- 409 D. Schumann, H. Schmid, Helv. Chim. Acta 46 (1963) 1996.
- 410 A.I. Scott, A.A. Qureshi, J. Am. Chem. Soc. 91 (1969) 5874.
- 411 K. Biemann, M. Spiteller-Friedmann, G. Spiteller, J. Am. Chem. Soc. 85 (1963) 631.
- 412 A. Walser, C. Djerassi, Helv. Chim. Acta 48 (1965) 391.
- 413 K. Aghoramurthy, R. Robinson, Tetrahedron 1 (1957) 172.
- 414 I.J. Levy, J.L. Men, M.M. Janot, Bull. Soc. Chim. Fr. 1960, 979.
- 415 P.N. Edwards, G.F. Smith, J. Chem. Soc. 1961, 152.
- 416 T.A. Henry, J. Chem. Soc. 1932, 2759.
- 417 M.F. Bartlett, B. Korzun, R. Sklar, A.F. Smith, W.I. Taylor, J. Org. Chem. 28 (1963) 1445.
- 418 M. Ito, C.C. Clark, M. Mortimore, J.B. Goh, S.F. Martin, J. Am. Chem. Soc. 123 (2001) 8003.
- 419 J.K. Treimer, M.H. Zenk, Eur. J. Biochem. 101 (1979) 225.
- 420 A.I. Scott, A.A. Qureshi, Tetrahedron 30 (1974) 2993.
- 421 A.I. Scott, C.C. Wei, Tetrahedron 30 (1974) 3003.
- 422 A.I. Scott, P.C. Cherry, C.C. Wei, Tetrahedron 30 (1974) 3013.
- 423 S.E. O'Connor, J.J. Maresh, Nat. Prod. Rep. 23 (2006) 532.
- 424T.M. Kutchan, Phytochem. 32 (1993) 493.
- 425 H. Rapoport, R.J. Windgassen, Jr., N.A. Hughes, T.P. Onak, J. Am. Chem. Soc. 82 (1960) 4404.
- 426 S.L. Lee, T. Hirata, A.I. Scott, Tetrahedron Lett. (1979) 691.
- 427 J.J. Maresh, L.-A. Giddings, A. Friedrich, E.A. Loris, S. Panjikar, B.L. Trout, J. Stoeckigt, B. Peters, S.E. O'Connor, J. Am. Chem. Soc. 130 (2008) 710.
- 428 L. Barleben, S. Panjikar, M. Ruppert, J. Koepke, J. Stoeckigt, Plant Cell 19 (2007) 2886.
- 429 D.I. Jacobs, M. Gaspari, J. van der Greef, R. van der Heijden, R. Verpoorte, Planta 211 (2005) 690.
- 430 M.M. Janot, Tetrahedron 14 (1961) 113.
- 431
M. Damak,
A. Ahond,
P. Potier,
M.M. Janot,
Tetrahedron Lett.
51
(1976)
4731.
10.1016/S0040-4039(00)93011-9 Google Scholar
- 432 A. Deiters, K. Chen, C.T. Eary, S.F. Martin, J. Am. Chem. Soc. 125 (2003) 4541.
- 433 S.F. Martin, K.X. Chen, C.T. Eary, Org. Lett. 1 (1999) 79.
- 434 D. Stauffacher, Helv. Chim. Acta 44 (1961) 2006.
- 435 A. Sandoval, F. Walls, J.N. Shoolery, J.M. Wilson, H. Budzikiewiez, C. Djerassi, Tetrahedron Lett. (1962) 409.
- 436 B. Gilbert, A.P. Duarte, Y. Nakagawa, J.A. Joule, S.E. Flores, J.A. Brissolese, J. Campello, E.P. Carrazzoni, R.J. Owellen, E.C. Blossey, K.S. Brown, Jr., C. Djerassi, C. Tetrahedron 21 (1965) 1141.
- 437 M. Zèches-Hanrot, N.-M. Nuzillard, B. Richard, H. Schaller, H.A. Hadi, T. Sévenet, L. LeMen-Olivier, Phytochem. 40 (1995) 587.
- 438 R. Iyengar, K. Schildknegt, M. Morton, J. Aube, J. Org. Chem. 70 (2005) 10645.
- 439 M. Hartmann, E. Schlittler, Helv. Chim. Acta 22 (1939) 547.
- 440 B. Witkop, J.B. Patrick, J. Am. Chem. Soc. 76 (1954) 5603.
- 441 H. Conroy, P.R. Brook, M.K. Rout, N. Silverman, J. Am. Chem. Soc. 79 (1957) 1763.
- 442
J.F.D. Mills,
S.C. Nyburg,
Tetrahedron Lett.
11
(1959)
1.
10.1016/S0040-4039(01)82748-9 Google Scholar
- 443
H. Conroy,
P.R. Brook,
Y. Amiel,
Tetrahedron Lett.
11
(1959)
4.
10.1016/S0040-4039(01)82749-0 Google Scholar
- 444
R. Robinson,
Tetrahedron Lett.
18
(1959)
14.
10.1016/S0040-4039(01)99994-0 Google Scholar
- 445 G. Stork, J.E. Dolfini, J. Am. Chem. Soc. 85 (1963) 2872.
- 446 B.M. Craven, D.E. Zacharias, Experientia 24 (1968) 770.
- 447 M.-M. Janot, H. Paourrat, J. LeMen, Bull. Soc. Chim. (France) 1954, 707.
- 448 W. Hofheinz, P. Schoenholzer, K. Bernauer, Helvetica Chim. Acta 59 (1976) 1213.
- 449 M.E. Kuehne, U.K. Bandarage, A. Hammach, Y.-L. Li, T. Wang, J. Org. Chem. 63 (1998) 2172.
- 450 S. Kobayashi, G. Peng, T. Fukuyama, Tetrahedron Lett. 40 (1999) 1519.
- 451 J. Murata, V. De Luca, Plant Journal 44 (2005) 581.
- 452 G.F. Smith, M.A. Wahid, J. Chem. Soc. 1963, 4002.
- 453 V.N. Kamat, J. de Sa, A. Vaz, F. Fernandes, S.S. Bhatnagar, Indian J. Med. Res. 46 (1958) 588.
- 454 N. Neuss, Bull. Soc. Chim. (France) 8/9 (1963) 1509.
- 455 W.D. Loub, N.R. Farnsworth, R.N. Blomster, W.W. Brown, Lloydia 27 (1964) 470.
- 456 A.I. Atta-ur-Rahman, M. Bashir, J. Nat. Prod. 47 (1984) 554.
- 457 M. Gorman, N. Neuss, K. Biemann, J. Am. Chem. Soc. 84 (1962) 1058.
- 458 J.W. Moncrief, W.N. Lipscomb, Acta Crystallogr. 21 (1966) 322.
- 459 J. Ruszkowska, R. Chrobak, J.K. Maurin, Z. Czarnocki, Acta Crystallogr. C60 (2004) o377.
- 460 A.E. Goodbody, T. Endo, J. Vukovic, J.P. Kutney, L.S. Choi, M.E. Misawa, Planta medica 54 (1988) 136.
- 461 T. Money, I.G. Wright, F. McCapra, E.S. Hall, A.I. Scott, J. Am. Chem. Soc. 90 (1968) 4144.
- 462 K.L. Stuart, J.P. Kutney, T. Honda, N.G. Lewis, B.R. Worth, Heterocycles 9 (1978) 647.
- 463 N. Nagabura, M. Rueffer, M.H. Zenk, J. Chem. Soc., Perkin Trans. 1, 9 (1972) 2308.
- 464 H. Ishikawa, D.L. Boger, J. Am. Chem. Soc. 128 (2006) 10596.
- 465 H. Ishikawa, D.A. Colby, S. Seto, P. Va, A. Tam, H. Kakei, T.J. Rayl, I. Hwang, D.L. Boger, J. Am. Chem. Soc. 131 (2009) 4904.
- 466 G. Büchi, K.E. Matsumoto, H. Nishimura, J.Am. Chem. Soc. 93 (1971) 3299.
- 467 A.R. Battersby, H. Gregory, J. Chem. Soc. 1963, 22.
- 468 W. Watt, R. Ghosh, T. Seal, B. Mukherjee, Acta Crystallogr. C49 (1993) 171.
- 469 A. Guggisberg, A.A. Gorman, B.W. Bycroft, H. Schmid, Helvetica Chim. Acta 52 (1969) 76.
- 470 D. Gagnon, C. Spino, J. Org. Chem. 74 (2009) 6035.
- 471 M.P. Cava, S.S. Tjoa, Q.A. Ahmed, A.I. DaRocha, J. Org. Chem. 33 (1968) 1055.
- 472 M.F. Bartlett, W.I. Taylor, M. Raymond-Hamet, Compt. Rend. Acad. Sci. 249 (1959) 1259.
- 473 M.F. Bartlett, W.I. Taylor, J. Am.Chem. Soc. 82 (1960) 5941.
- 474
M.F. Bartlett,
W.I. Taylor,
Tetrahedron Lett.
20
(1959)
20.
10.1016/S0040-4039(01)99479-1 Google Scholar
- 475 O. Strouf, J. Trojanek, Coll. Czech. Chem. Comm. 29 (1964) 447.
- 476 C. Szantay, L. Szabo, G. Kalaus, Tetrahedron Lett. (1973) 2.
- 477 J.P. Kutney, J.F. Beck, V.R. Nelson, R.S. Sood, J. Am. Chem. Soc. 93 (1971) 255.
- 478 N. Neuss, M. Gorman, Tetrahedron Lett. (1961) 206.
- 479 W. Runguphan, S.E. O'Connor, Nature Chem. Bio. 5 (2009) 151.
- 480 D.F. Dickel, C.L. Holden, R.C. Maxfield, L.E. Paszek, W.I. Taylor, J. Am. Chem. Soc. 80 (1958) 123.
- 481 N. Neuss, Bull. Soc. Chim. Fr. 8/9 (1963) 1509.
- 482 A.E. Goodbody, T. Endo, J. Vukovic, J.P. Kutney, L.S. Choi, M. Misawa, Planta medica 54 (1988) 136.
- 483 L. Moisan, P. Thuery, M. Nicolas, E. Doris, B. Rousseau, Angew. Chem. Int. Ed. 45 (2006) 5334.
- 484 M. Gorman, N. Neuss, Annali di Chimica (Rome) 53 (1963) 43.
- 485 D.V. Basile, M.S. Punch, J. Pablo, B. Brenner, W.L. Hearn, D.C. Mash, Nat. Prod. Lett. 13 (1999) 233.
- 486 M.F. Bartlett, D.F. Dickel, W.I. Taylor, J. Am. Chem. Soc. 80 (1958) 126.
- 487 J.D. White, Y. Choi, Org. Lett. 2 (2000) 2373.
- 488 J.D. White, Y. Choi, Helv. Chim. Acta 85 (2002) 4306.
- 489 R. Goutarel, F. Percheron, J. Wohlfahrt, M.M. Janot, Ann. Pharmaceutiques Francaises 15 (1957) 353–360.
- 490 P. James, J.P. Kutney, F. Bylsma, Helv. Chim. Acta 58 (1975) 1672.
- 491 P. Rosenmund, W.H. Haase, J. Bauer, R. Frische, Chem. Ber. 108 (1975) 1871.
- 492 B.M. Trost, S.A. Godleski, J.P. Genet, J. Am. Chem. Soc. 100 (1976) 3930.
- 493 J.P. Kutney, R.T. Brown, E. Riers, Can. J. Chem. 43 (1965) 1545.
- 494 M.J. Hoizey, Phytochem. 13 (1974) 1995.
- 495 M.J. Hoizey, C. Sigaut, M.J. Jacquier, L. Le Men-Olivier, J. Levy, J. Le Men, Tetrahedron Lett. 17 (1974) 1601.
- 496 J. Le Men, G. Hugel, M. Zeches, M.J. Hoizey, L. Le Men-Olivier, J. Levy, Compt. Rend. Acad. Sci. 283 (1976) 759.
- 497 N. Neuss, M. Gorman, H.E. Boaz, N.J. Cone, J. Am. Chem. Soc. 84 (1962) 1509.
- 498 N. Neuss, L.L. Huckstep, N.J. Cone, Tetrahedron Lett. (1967) 811.
- 499 J.P. Kutney, F. Bylsma, Helv. Chim. Acta 58 (1975) 1672.
- 500 G.R. Eccles, Proc. Amer. Pharm. Assoc. 84 (1888) 382.
- 501 C.-Y. Gan, W.T. Robinson, T. Etoh, M. Hayashi, K. Komiyama, T.-S. Kam, Org. Lett. 11 (2009) 3962.
- 502 H.F. Hodson, B. Robinson, S.F. Smith, Proc. Chem. Soc. (London) 1961, 465.
- 503
R.H.F. Manske,
L. Marion,
Can. J. Res.
17B
(1939)
293.
10.1139/cjr39b-041 Google Scholar
- 504 J.B. Hendrickson, R. Goeschke, R. Rees, Tetrahedron 20 (1964) 565.
- 505 J.T. Link, J.E. Overman, J. Am. Chem. Soc. 118 (1996) 8166.
- 506 M. Movassaghi, M. Schmidt, Angew. Chem. Int. Ed. 46 (2007) 3725.
- 507 G. Bifulco, I. Bruno, R. Riccio, J. Nat. Prod. 63 (2000) 447.
- 508 B. Bao, Q. Sun, X. Yao, J. Hong, C.-O. Lee, H.Y. Cho, J.H. Jung, J. Nat. Prod. 70 (2007) 2.
- 509 X. Guinchara, Y. Vallée, J.-N. Denis, J. Org. Chem. 72 (2007) 3972.
- 510 N.S. Burres, D.A. Barber, S.P. Gunasekera, L.L. Shen, J.J. Clement, Biochem. Pharmacology 42 (1991) 745.
- 511 S.P. Gunasekera, P.J. McCarthy, M. Kelly-Borges, J. Nat. Prod. 57 (1994) 1437.
- 512 T. Kouko, K. Matsumura, T. Kawasaki, Tetrahedron 61 (2005) 2309.
- 513 X. Guinchara, Y. Vallée, J.-N. Denis, Org. Lett. 9 (2007) 3761.
- 514 R.L. Noble, D.T. Beer, J.H. Cutts, Ann. N.Y. Acad. Sci. 76 (1958) 659.
- 515 M. Gorman, N. Neuss, K. Biemann, J. Am. Chem. Soc. 24 (1962) 1058.
- 516 J.W. Moncrief, W.N. Libscomb, Acta Crystallogr. 21 (1966) 311.
- 517 I.S. Johson, H.F. Wright, G.H. Svoboda, Abstracts of the Proc. Am. Assoc.for Cancer Research 3 (1962) 4.
- 518 S. Yokoshima, T. Ueda, S. Kobayashi, A. Sato, T. Kuboyama, H. Tokuyama, T. Fukuyama, J. Am. Chem. Soc. 124 (2002) 2137.
- 519 P. Mangeney, A.R. Zo, N. Langlois, Y. Langlois, P. Potier, J. Am. Chem. Soc. 101 (1979) 2243.
- 520 H. Tanaka, H. Matsushima, A. Nishibu, B.E. Clausen, A. Takashima, Cancer Res. 69 (2009) 6987.
- 521 A. Bräuninger, R. Schmitz, D. Bechtel, C. Renné, M.L. Hansmann, R. Küppers, Int. J. Cancer 118 (2006) 1853.
- 522 J.W. Moncrief, W.N. Lipscomb, J. Am. Chem. Soc. 87 (1965) 4963.
- 523 G.H. Svoboda, J. Nat. Prod. (Lloydia) 24 (1961) 173.
- 524 T.S. Giani, Pharmacognosy Rev. 1 (2007) 203.
- 525 J.B. Caventou, P.J. Pelletier, Annalas. de Chimie (Cachan, France) 15 (1820) 291, 360.
- 526 R.B. Woodward, W.E. Doering, J. Am. Chem. Soc. 67 (1945) 860.
- 527 J.I. Seeman, Angew. Chem. Int. Ed. 46 (2007) 1378.
- 528 P. Rabe Ber. Dtsch. Chem. Ges. 41 (1908) 62.
- 529
O. Hesse,
Ber. Dtsch. Chem. Ges.
4
(1871)
818.
10.1002/cber.18710040293 Google Scholar
- 530 S.S. Handa, S.K. Gupta, K. Vasisht, A.T. Keene, J.D. Phillipson, Planta medica 50 (1984) 358.
- 531 M. Ihara, N. Taniguchi, K. Noguchi, K. Fukumoto, T. Kametani, J. Chem. Soc., Chem. Commun. 1986, 573.
- 532
Van Hejningen,
Liebig's Ann.
72
(1849)
301.
10.1002/jlac.18490720332 Google Scholar
- 533 G. Grethe, H.L. Lee, T. Mitt, M.R. Uskokovic, J. Am. Chem. Soc. 100 (1978) 589.
- 534 G. Schneider, W. Kleinert, Planta Med. 22 (1972) 109.
- 535 M.E. Wall, M.C. Wani, C.E. Cook, K.H. Palmer, A.T. McPhail, G.A. Sim, J. Am. Chem. Soc. 88 (1966) 3888.
- 536 C.J. Thomas, N.J. Rahier, S.M. Hecht, Bioorg. Med. Chem. 12 (2004) 1585.
- 537 C.R. Hutchinson, A.H. Heckendorf, P.E. Daddona, E. Hagaman, E. Wenkert, J. Am. Chem. Soc. 96 (1974) 5609.
- 538 A.H. Heckendorf, C.R. Hutchinson, Tetrahedron Lett. (1977) 4153.
- 539 C.R. Hutchinson, A.H. Heckendorf, J.L. Straughn, P.E. Daddona, D.E. Cane, J. Am. Chem. Soc. 101 (1979) 3358.
- 540 S. Dallavalle, L. Merlini in E. Fattorusso, O. Taglialatela-Scafati (eds.): Modern Alkaloids, Wiley-VCH, Weinheim 2008, p. 503ff.
- 541
E. Braitmaier:
Terpenes,
Wiley-VCH,
Weinheim
2006.
10.1002/9783527609949 Google Scholar
- 542 E. Pichersky, J. Gershonzon, Curr. Opin. Plant Biol., 5 2002, 237.
- 543 M. Rohmer, Nat. Prod. Rep. 16 (1999) 565.
- 544 W. Eisenreich, M. Schwarz, A. Cartayrade, D. Arigoni, M.H. Zenk, A. Bacher, Chem. Biol. 5 (1998) R221.
- 545 M.L. Ginger, M.L. Chance, I.H. Sadler, L.J. Goad, J. Biol. Chem. 276 (2001) 11674.
- 546 Y. Boucher, W.F. Doolittle, Mol. Microbiol. 37 (2000) 703.
- 547 B.M. Lauge, T. Rujan, W. Martin, R. Croteam, PNAS 97 (2000) 13172.
- 548 H.K. Lichtenthaler, Biochem. Soc. Trans. 28 (2000) 785.
- 549 J. Zeidler, J. Schwender, C. Muller, J. Wiesner, C. Wiedemeyer, E. Beck, H. Jomaa, H.K. Lichtenthaler, Z. Naturforsch. 53 (1998) 980.
- 550 T.J. Bach, H.K. Lichtenthaler, Z. Naturforsch. 37 (1982) 46.
- 551
A. Jux,
G. Gleixner,
W. Boland,
Angew. Chem. Int. Ed.
40
(2001)
2091.
10.1002/1521-3773(20010601)40:11<2091::AID-ANIE2091>3.0.CO;2-5 CAS PubMed Web of Science® Google Scholar
- 552 D. Arigoni, W. Eisenreich, C. Latzel, S. Sagner, T. Radykewicz, M.H. Zenk, A. Bacher, PNAS 96 (1999) 1309.
- 553 G. Massé, S.T. Belt, S.J. Rowland, M. Rohmer, Proc. Natl. Acad. Sci. USA 101 (2004) 4413.
- 554 M. Lange, T. Rujan, W. Martin, R. Croteau, PNAS, 97 (2000) 13172.
- 555 Y. Boucher, W.F. Doolittle, Mol. Microbiol. 37 (2000) 703.
- 556 J.E. Barquera-Lozada, G. Cuevas, J. Org. Chem. 74 (2009) 874.
- 557 L. Wessjohann, S. Zakarova, D. Schulze, J. Kufka, R. Weber, L. Braeuer, W. Brandt, Chimia 63 (2009) 340.
- 558 J. Kirby, J.D. Kesling, Ann. Rev. Plant Biol. 60 (2009) 335.
- 559 D. Tholle, Curr. Opin. Plant Biol. 9 (2006) 297.
- 560 S.C. Trapp, R.B. Croteau, Genetics 158 (2001) 811.
- 561 J. Bohlmann, J. Gershenzon, Proc. Nat. Acad. Sci. 106 (2009) 10402.
- 562 F. Chen, D.-K. Ro, J. Petri, J. Bohlmann, E. Pichersky, D. Tholl, Plant Physiol. 135 (2004) 1956.
- 563 P.P.W. Huber, R.N. Philippe, K.-A. Godard, R.N. Sturrock, J. Bohlmann, Phytochem 66 (2005) 1427.
- 564 N.J. Nieuwenhuizen, M.Y. Yang, A.J. Matich, S.A. Green, X. Chen, Y.-K. Yauk, L.L. Beuning, D. Nagegowda, N. Dudareva, R.G. Atkinson, J. Exp. Bot. 60 (2009) 3203.
- 565 L. Tang, F. Tang, J. Duan, Y. Lin, Q. Zhong, Linye Kexue 45 (2009) 11 (CA required).
- 566 B.T. Greenhagen, P.E. O'Maille, J.P. Noel, J. Chappell, PNAS 103 (2006) 9826.
- 567 P.R. Wilerman, R.J. Peters, J. Amer. Chem. Soc. 129 (2007) 15736.
- 568 C.A. Lesburg, G. Zhai, D.E. Cane, D.W. Christianson, Science 277 (1997) 1820.
- 569 M. Ashby, P.E. Edwards, J. Biol. Chem. 265 (1990) 13157.
- 570 S. Green, C.J. Squire, N.J. Nieuwenhuizen, E.N. Baker, W. Laing, J. Biol. Chem. 284 (2009) 8661.
- 571 T.G. Köllner, C. Schnee, J. Gershenzon, J. Degenhardt, Plant Cell 16 (2004) 1115.
- 572 K. Zhou, R.J. Peters, Phytochem. 70 (2009) 366.
- 573 S.A. Agger, F. Lopez-Gallego, T.R. Hoye, C. Schmidt-Dannert, J. Bacteriol. 190 (2008) 6084.
- 574 D.A. Nagegowda, M. Gutensohn, C.G. Wilkerson, N. Dudareva, Plant Journal 55 (2008) 224.
- 575 S. Lee, J. Chappell, Plant Physiol. 147 (2008) 1017.
- 576 T.G. Köllner, C. Schnee, S. Li, A. Svatos, B. Scheider, J. Gershenzon, J. Degenhart, J. Biol. Chem. 283 (2008) 20779.
- 577 D. Koepke, R. Schroeder, H.M. Fischer, M. Hanna, J. Gershenzon, M. Hilker, A. Schmidt, Planta 228 (2008) 427.
- 578 Y. Yoshikuni, J.A. Dietrich, F.F. Nawroozi, P.C. Babbitt, J.D. Kiesling, Chem. Biol. 15 (2008) 607.
- 579 D. Matthews, H. Jones, P. Gans, S. Coates, L.M.J. Smith, J. Agric. Food Chem. 53 (2005) 7766.
- 580 R.S. van der Hoeven, A.J. Monforte, D. Breeded, S.D. Tanksley, J.C. Steffens, Plant Cell 12 (2000) 2283.
- 581 J.W. Cornforth, I.Y. Gore, G. Popjak, Chem. Biol. 65 (1957) 94.
- 582 J. McMurry, T. Begley: The Organic Chemistry of Biological Pathway, Roberts & Co., Englewood 2005, p. 125.
- 583 A. Tait, L.C. Hodge, K.B. Eiknas, J. Steroid Biochem. 26 (1987) 99.
- 584 A. Aharoni, M.A. Jongsma, T.-Y. Kim, M.-B. Ri, A.P. Giri, F.W.A. Verstappen, W. Schwab, H.J. Bouwmeester, Phytochem. Rev. 5 (2006), 47.
- 585 G.A. Cordell: The Alkaloids, vol. 52, Academic Press, New York 1999, p. 261.
- 586 R.B. Herbert, Alkaloids (London) 1983, 1.
- 587 D. Gross, W. Berg, H.R. Schuette, Biochemie und Physiologie der Pflanzen 162 (1972) 576.
- 588 E.M. Dickinson, G. Jones, Tetrahedron 25 (1969) 1523.
- 589 D.A. Ockey, M.A. Lewis, N.E. Schore, Tetrahedron 59 (2003) 5377.
- 590 L. Costantino, A.P. Lins, D. Barlocco, F. Celotti, S.A. El-Abady, T. Brunetti, R. Maggi, L. Antolini, Pharmazie 58 (2003) 140.
- 591 J.-J. Fu, H-Z. Jin, Y-H. Shen, W-D. Zhang, W-Z. Xu, Q. Zeng, S-K. Yan, Helv. Chim. Acta 90 (2007) 2151.
- 592 N. Robert, C. Hoarau, F. Marsais, Tetrahedron 63 (2007) 3702.
- 593 T. Sakan, F. Murai, Y. Hayashi, Y. Honda, T. Shono, M. Nakajima, M. Kato, Tetrahedron 23 (1967) 4635.
- 594 G.H. Harris, E.C. Fixman, F.R. Stermitz, L. Castedo, J. Nat. Prod. 51 (1988) 543.
- 595 B. Schöllhorn, J. Mulzer, Eur. J. Org. Chem. 4 (2006) 901.
- 596 M. Ernst, G. Helmchen, Synthesis 2002, 1953.
- 597 C.G. Casinovi, F. Delle Monache, G.B. Marini-Bettolo, E. Bianchi, J. Garbarino, Gazz. Chim. Ital. 92 (1962) 92 479.
- 598 W. Oppolzer, E.J. Jacobsen, Tetrahedron Lett. (1986) 1141.
- 599 T. Tsunoda, F. Ozaki, N. Shirakata, Y. Tamaoka, H. Yamamoto, S. Ito, Tetrahedron Lett. (1996) 2463.
- 600 E.J. Eisenbraun, H.H. Appel, Chem. Ind. (London) 1962, 1242.
- 601 H. Auda, G.R. Waller, E.J. Eisenbraun, J. Biol. Chem. 242 (1967) 4157.
- 602 K. Jones, M.L. Escudero-Hernandez, Tetrahedron 54 (1998) 2275.
- 603 J.-L. Boeve, S. Heilporn, Biochem. Systematics and Ecology 36 (2008) 836.
- 604 J.W. Miyazawa, J. Kawata, J. Essential Oil Res. 18 (2006) 508.
- 605 J.W. Wheeler, T. Olagbemiro, A. Nash, M.S. Blum, J. Chem. Ecology 3 (1977) 241.
- 606 T. Sakan, A. Fujino, F. Murai, A. Suzui, Y. Butsugan, Bull. Chem. Soc. (Japan) 32 (1959) 1155.
- 607 M. Ganzera, S. Crockett, M.R. Tellez, I. Khan, Die Pharmazie 56 (2001) 896.
- 608 J.E. Feaster, M.A. Scialdone, R.G. Todd, Y.I. Gonzalez, J.P. Foster, D. Hallahan, J. Med. Entomology 46 (2009) 832.
- 609 C.J. Peterson, J. Ems-Wilson, J. Economic Entomology 96 (2003) 1275.
- 610 M. Kigawa, M. Tanaka, H. Mitsuhashi, T. Wakamatsu, Heterocycles 33 (1992) 117.
- 611 T.R. Govindachari, K. Nagarajan, S. Rajappa, Cell. Molec. Life Sci., 14 (1958) 5.
- 612 E. Leete, Science 147 (1965) 1000.
- 613 E.M. Nobrega, A.A. Craveiro, J.T. Welch, T. Nicolson, J.A. Zubieta, J. Nat. Prod. 51 (1988) 962.
- 614 M. Frederich, M.-J. Jacquier, P. Thepenier, P. De Mol, M. Tits, G. Philippe, C. Delaude, L. Angenot, M. Zeches-Hanrot, J. Nat. Prod. 65 (2002) 1381.
- 615 T.R. Govindachari, K. Nagarajan, S. Rajappa, J. Chem. Soc. 1957, 2725.
- 616 T.U. Rakhmatullaev, S.T. Akramov, S. Yunusov, S. Yu, Khim. Prir. Soedin. 1969, 5.
- 617
A. Abdusamatov,
Khim. Prir. Soedin.
12
(1976),
122;
Chem. Nat. Compd. (Engl. Trans.)
12
(1976),
116.
10.1007/BF00570229 Google Scholar
- 618 B.T. Shaneberg, D.K. Green, A.T. Sneden, J. Nat. Prod. 64 (2001) 624.
- 619 H. Duan, Y. Takaishi, H. Momota, Y. Ohmoto, T. Taki, Y. Jia, D. Li, J. Nat. Prod. 64 (2001) 582.
- 620 O. Shirota, H. Morita, K. Takeya, H. Itokawa, Heterocycles 38 (1994) 383.
- 621 R.T. LaLonde, C.F. Wong, K.C. Das, J. Amer. Chem. Soc. 95 (1973) 6342.
- 622 H. Matsuda, K. Yoshida, K. Miyagawa, Y. Nemoto, Y. Asao, M. Yoshikawa, Bioorg. Med. Chem. Lett. 16 (2006) 1567.
- 623 H. Matsuda, T. Morikawa, M. Oda, Y. Asao, M. Yoshikawa, Bioorg. Med. Chem. Lett. 13 (2003) 4945.
- 624
V.T. de Araújo-Júniora,
M.S. da Silva,
E.V. Leitão da-Cunha,
M. de Fátima
Agra,
P.F. de Athayde-Filho,
I.J. Curcino Vieira,
R. Braz-Filhoc,
J.M. Barbosa-Filho,
J. Braz. Chem. Soc.
16
(2005)
553–557.
10.1590/S0103-50532005000400010 Google Scholar
- 625 C. Didier, D.J. Critcher, N.D. Walshe, Y. Kojima, Y. Yamauchi, A.G.M. Barrett, J. Org. Chem. 69 (2004) 7875.
- 626 H. Itokawa, O. Shirota, H. Morita, K. Takeya, Heterocycles 34 (1992) 885.
- 627 O. Shirota, H. Morita, K. Takeya, H. Itokawa, Heterocycles 38 (1994) 383.
- 628 D.A. Perry, H. Maeda, J. Tone, GB 3240100, 1991.
- 629 Pfizer, WO 9519363, 1995 (Y. Kojima, H. Yameuchi, N. Kojima, B.F. Bishop).
- 630 R.T. LaLonde, C.F. Wong, K.C. Das, J. Amer. Chem. Soc. 95 (1973) 6342.
- 631 L.M. Liao, Alkaloids 60 (2003) 287.
- 632 M. Katoh, M. Mizutani, T. Honda, Heterocycles 69 (2006) 193.
- 633 D. Craig, G.D. Henry, Eur. J. Org. Chem. 16 (2006) 3558.
- 634 J. Gebauen, S. Blechert, SYNLETT 2005, 2826.
- 635 D. Tholl, Curr. Opinion Plant Biol. 9 (2006) 297.
- 636 F. Min, W. Meng, W. Ji-Feng, Q. Yan-Jiang, W. Zhao, Biochem. Biophys. Res. 354 (2007) 929.
- 637 G.Y. Zuo, H.P. He, B.G. Wang, X. Hong, Y.M. Hu, X.J. Hao, Chin. Chem. Lett. 14 (2003) 383.
- 638 X. Hao, Y. Shen, L. Li, H. He, Curr. Med. Chem. 10 (2003) 2253.
- 639 P.-J. Zhao, S. Gao, L.-M. Fan, J.-L. Nie, H.-P. He, Y.-M. Shen, X.-J. Hao, J. Nat. Prod. 72 (2009) 645.
- 640 W. Nagata, T. Sugasawa, M. Narisada, T. Wakabayashi, Y. Hayase, J. Amer. Chem. Soc. 89 (1967) 1483.
- 641 X.-J. Hao, M. Node, T. Taga, Y. Miwa, J. Zhou, S.-Y. Chen, K. Fuji, Chem. Pharm. Bull. 35 (1987) 1670.
- 642 M.C. Wani, H.L. Taylor, M.E. Wall, P. Coggon, A.T. McPhail, J. Amer. Chem. Soc. 93 (1971) 2325.
- 643 B.R. Goldspiel, Pharmacotherapy 17 (1995) 1105.
- 644 P.E. Fleming, H.G. Floss, M. Haertel, A.R. Knagg, A. Lanning, U. Mocek, K.D. Walker, Pure & Appl. Chem. 66 (1994) 2045.
- 645 W. Eisenreich, B. Menhard, P.J. Hylands, H.Z. Meinhart, Proc. Natl. Acad. Sci. 93 (1996) 6431.
- 646 S. Jennewein, R. Croteau, Appl. Microbiol. Biotechnol. 57 (2001) 13.
- 647 Q. Huang, C.A. Roessner, R. Croteau, A.I. Scott, Bioorg. Med. Chem. 9 (2001) 2237.
- 648 A. Stierle, G. Strobel, D. Stierle, P. Grothaus, G. Bignami, J. Nat. Prod. 58 (1995) 1315.
- 649 A. Stierle, G. Strobel, D. Stierle, Science 1993, 260.
- 650 D.P. Zhou, W.X. Ping, J.Q. Sun, A.H. Zhou, X.L. Liu, J. Microbiol. 21 (2001) 8.
- 651 D.P. Zhou, J.Q. Sun, N.Y. Yu, W.X. Ping, X.Q. Zheng, Mycosystema 20 (2001) 277.
- 652 Y. Chi, D.-L. Zhao, D.-P. Zhao, World J. Microbiol. Biotechnol. 24 (2008) 2601.
- 653 G. Yao, T.P. Kondratyuk, G.T. Tan, J.M. Pezzuto, L.C. Chang, J. Nat. Prod. 72 (2009) 319.
- 654 G. Yao, L.C. Chang, Org. Lett. 9 (2007) 3037.
- 655 K. Ueda, D. Uemura, Studies in Nat. Prod. Chem. 2008, 57.
- 656 V.M. Dembitzky, T.A. Gloriotsova, V.V. Poroikov, Mini Rev. Med. Chem. 5 (2005) 319.
- 657 C. Dan, Y. Zhou, D. Ye, S. Peng, L. Ding, M.L. Gross, S.X. Qiu, Org. Lett. 9 (2007) 1813.
- 658 M.T. Liu, S. Lin, Y.-H. Wang, W. He, S. Li, S.-L. Wang, Y.-C. Yang, J.-G. Shi, Org. Lett. 9 (2007) 129.
- 659 A.I. Atta-ur-Rahman, M.I. Choudhary, The Alkaloids, vol. 50, Academic Press, New York 1998, p. 61ff.
- 660 H.-J. Li, Y. Jiang, P. Li, Nat. Prod. Rep. 23 (2006) 735.
- 661 D.M. Harrison, Nat. Prod. Rep. 27 (1990) 139.
- 662 B.R. Moser, J. Nat. Prod. 71 (2008) 487.
- 663 B.P. Bhavandan, G.P. Wannigama, J. Chem. Soc. 1960, 2368.
- 664 S. Terada, K. Hayashi, H. Mitsuhashi, Chem. Pharm. Bull. 25 (1977) 2802.
- 665 J.W. Daly, B. Witkop, P. Bommer, K. Biemann, J. Amer. Chem. Soc. 87 (1965) 124.
- 666 H. Auterhoff, F. Gunther, Archiv Pharm. Ber. Deutschen Pharm. Ges. 288 (1955) 455.
- 667 G.R. Pettit, M. Inoue, Y. Kamano, D.L. Herald, C. Arm, C. Dufresne, N.D. Schmidt, J.M. Doubek, T.S. Krupa, J. Amer. Chem. Soc. 110 (1988) 2006.
- 668 T.G. Lacour, C. Guo, S. Bhandaru, M.R. Boyd, P.L. Fuchs, J. Amer. Chem. Soc. 120 (1998) 692.
- 669 A. Kohara, C. Nakajima, K. Hashimoto, T. Ikenaga, H. Tanaka, Y. Shoyama, S. Yoshida, T. Murinaka, Plant Mol. Biol. 57 (2005) 225.
- 670 A. Kohara, C. Nakajima, S. Yoshida, T. Muranaka, Phytochemistry 68 (2007) 478.
Further Reading
- T. Aniszewski: Alkaloids - Secrets of Life, Elsevier, Amsterdam 2007.
-
J. Buckingham,
K. H. Baggaley,
A. D. Roberts,
L. F. Szabo (eds.):
Dictionary of Alkaloids,
2nd ed.,
CRC Press,
Boca Raton, FL
2010.
10.1201/EBK1420077698 Google Scholar
- G. A. Cordell (ed.): The Alkaloids, vol. 68, Academic Press, San Pedro, CA 2010.
- D. R. Dalton, L. M. Mascavage, M. Wilson: Alkaloids, Kirk Othmer Encyclopedia of Chemical Technology, 5th edition, vol. 2, p. 71–113, John Wiley & Sons, Hoboken, 2004, online: DOI: 10.1002/0471238961.0112110104011220.a01.pub2 (January 2003).
- E. Fattorusso, O. Taglialatela-Scafati (eds.): Modern Alkaloids, Wiley-VCH, Weinheim 2008.
-
C. E. Song (ed.):
Cinchona Alkaloids in Synthesis and Catalysis,
Wiley-VCH,
Weinheim
2009.
10.1002/9783527628179 Google Scholar
